Canmetcon
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Record Information
Version2.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2014-12-24 20:24:38 UTC
Accession NumberT3D1787
Identification
Common NameBromomethane
ClassSmall Molecule
DescriptionBromomethane (or methyl bromide) is an organobromide compound that may be produced both synthetically and by naturally marine organisms and certain terrestrial plants. It was used extensively as a pesticide and as a fire extinguisher component until being phased out by most countries in the early 2000s, as it is considered an ozone-depleting substance. The primary use of methyl bromide is/was as a fumigant in soil to control fungi, nematodes, and weeds; in space fumigation of food commodities (e.g., grains); and in storage facilities (such as mills, warehouses, vaults, ships, and freight cars) to control insects and rodents. Its popularity as a fumigant is largely attributable to its high toxicity to many pests, the variety of settings in which it can be applied, its ability to penetrate the fumigated substances, and its rapid dissipation following application. Trace amounts of methyl bromide have been detected in drinking water. There are many reports of humans who have died following acute inhalation exposure to bromomethane. Most cases have involved accidental exposures associated with manufacturing or packaging operations, use of fire extinguishers containing bromomethane, or fumigation activities. Death is not immediate, but usually occurs within l-2 days of exposure. The cause of death is not certain, but is probably due to neurological and lung injury.
Compound Type
  • Bromide Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organobromide
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Bercema
BMM
Brom-methan
Brom-O-gas
Brom-O-gas methyl bromide soil fumigant
Brom-O-gaz
Brom-O-sol
Brommethan
Bromo-Methane
Bromometano
Bromur di metile
Bromure de methyle
Bromuro di metile
Broommethaan
Celfume
CH3Br
Chlorodibromomethane
Curafume
Dawson 100
Detia gas ex-m
Dow Fume MC2
Dowfume
Dowfume mc-2
Dowfume MC-2 Fumigant
Dowfume mc-2 soil fumigant
Dowfume MC-2R
Dowfume mc-33
Drexel plant bed gas
EDCO
Embafume
Fumigant-1
Fumigant-1 (Obs.)
Halon 1001
Haltox
Iscobrome
Kayafume
M-b-c Fumigant
MB
MBC soil fumigant
Mbc-33 Soil Fumigant
MBX
Meb R
MEBR
Merth-O-gas
Metafume
Meth-O-gas
Methogas
Methyl bromide
Methyl bromide as a structural fumigant
Methyl bromide rodent fumigant (with chloropicrin)
Methyl bromide, 14C-labeled
Methyl bromide, BSI, ISO, JMAF
Methyl fume
Methylbromid
Methylbromide
Metylu bromek
Monobrommethan
Monobromomethane
Pestmaster
Pestmaster (obs.)
Pestmaster Soil Fumigant-1
Profume
Profume (obs.)
R 40B1
Rfdfif@
Rotox
Superior Methyl Bromide-2
Terabol
Terr-O-cide II
Terr-O-gas
Terr-O-gas 100
Terr-O-gas 67
Tri-brom
Zytox
Chemical FormulaCH3Br
Average Molecular Mass94.939 g/mol
Monoisotopic Mass93.942 g/mol
CAS Registry Number74-83-9
IUPAC Namebromomethane
Traditional Namemethyl bromide
SMILESCBr
InChI IdentifierInChI=1S/CH3Br/c1-2/h1H3
InChI KeyInChIKey=GZUXJHMPEANEGY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassHalomethanes
Direct ParentHalomethanes
Alternative Parents
Substituents
  • Halomethane
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateGas
AppearanceColorless gas.
Experimental Properties
PropertyValue
Melting Point-93.7°C
Boiling PointNot Available
Solubility15.2 mg/mL at 25°C
LogP1.19
Predicted Properties
PropertyValueSource
Water Solubility28.6 g/LALOGPS
logP0.68ALOGPS
logP1.02ChemAxon
logS-0.52ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.3 m³·mol⁻¹ChemAxon
Polarizability5.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-745f8b23626d21db04f3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-745f8b23626d21db04f3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9000000000-7942af0aaf6970a66f15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-489f85dffd44526b6fafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-489f85dffd44526b6fafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-489f85dffd44526b6fafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-8cbdea03c774de7d15baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-8cbdea03c774de7d15baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8cbdea03c774de7d15baView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-169ac2e004c3655205b0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (19) ; inhalation (19) ; dermal (19)
Mechanism of ToxicityOrganobromide compounds such as bromomethane are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. The bromide ion (which is produced from bromomethane metabolism in the body) is known to affect the central nervous system, causing a condition called bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (19, 20, 15). However, the exact mechanism of toxicity for methyl bromide is currently uncertain, although its alkylating property as well as the reactive intermediates formed through metabolic transformation remain attractive hypotheses.
MetabolismBromomethane undergoes initial metabolism primarily by nucleophilic displacement of the bromide ion. When the attacking species is water, the products are methanol and bromide ion. Bromomethane may also react with organic thiols (R-SH) to yield S-methyl derivatives. This has been shown to result in formation of S-methylcysteine derivatives in hemoglobin of mice exposed to bromomethane. Further metabolism of methanol or S-methyl derivatives then leads to the formation of carbon dioxide.
Toxicity ValuesLD50: 214 mg/kg (Oral, Rat) (14) LD50: 1540 mg/m3 over 2 hours (Inhalation, Mouse) (14)
Lethal DoseLethality has been reported in humans following exposure to 60,000 ppm for 2 hours and 1,600-8,000 ppm for 4-6 hours.
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (21)
Uses/SourcesThe primary use of methyl bromide is as a fumigant in soil to control fungi, nematodes, and weeds; in space fumigation of food commodities (e.g., grains); and in storage facilities (such as mills, warehouses, vaults, ships, and freight cars) to control insects and rodents. In most places, levels of methyl bromide in the air are usually < 0.025 parts per billion (ppb). Industrial areas have higher levels (ranging up to 1.2 ppb) because of releases from chemical factories. Workers who fumigate homes and fields may be exposed to high levels of methyl bromide if proper safety precautions are not followed.
Minimum Risk LevelNot Available
Health EffectsBromomethane is highly toxic. Studies in humans indicate that the lung may be severely injured by the acute (short-term) inhalation of bromomethane. Acute and chronic (long-term) inhalation of bromomethane can lead to neurological effects in humans. Neurological effects have also been reported in animals. Degenerative and proliferative lesions in the nasal cavity developed in rats chronically exposed to bromomethane by inhalation. Chronic inhalation exposure of male animals has resulted in effects on the testes at high concentrations. Studies in humans indicate that the lung may be most severely injured by the acute inhalation exposure of bromomethane. The kidney is also sensitive to bromomethane. Anuria and proteinuria are common signs of renal injury in acutely exposed humans.
SymptomsBreathing modest amounts of bromomethane may lead to the development of a headache, nausea and weakness after several hours. Breathing high concentrations of bromomethane may cause pulmonary edema, impairing respiratory function. Acute exposure by inhalation of bromomethane frequently leads to neurological effects in humans. Symptoms of acute exposure in humans include headaches, dizziness, fainting, apathy, weakness, confusion, speech impairment, visual effects, numbness, twitching, and tremors; in severe cases paralysis and convulsions are possible. Bromomethane is irritating to the eyes, skin, and mucous membranes of the upper respiratory tract. Dermal exposure to bromomethane can cause itching, redness, and blisters in humans. Neurological effects, including lethargy, forelimb twitching, tremors, and paralysis, have also been observed after chronic exposure to bromomethane.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31524
PubChem Compound ID6323
ChEMBL IDCHEMBL48339
ChemSpider ID6083
KEGG IDC18447
UniProt IDNot Available
OMIM ID
ChEBI ID39275
BioCyc IDCPD0-1304
CTD IDC005218
Stitch IDBromomethane
PDB IDBMM
ACToR ID848
Wikipedia LinkBromomethane
References
Synthesis ReferenceNot Available
MSDST3D1787.pdf
General References
  1. Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
  2. Zhao RS, Lao WJ, Xu XB: Headspace liquid-phase microextraction of trihalomethanes in drinking water and their gas chromatographic determination. Talanta. 2004 Mar 10;62(4):751-6. doi: 10.1016/j.talanta.2003.09.035. [18969359 ]
  3. Mouly D, Joulin E, Rosin C, Beaudeau P, Zeghnoun A, Olszewski-Ortar A, Munoz JF, Welte B, Joyeux M, Seux R, Montiel A, Rodriguez MJ: Variations in trihalomethane levels in three French water distribution systems and the development of a predictive model. Water Res. 2010 Oct;44(18):5168-79. doi: 10.1016/j.watres.2010.06.028. Epub 2010 Jun 19. [20663536 ]
  4. Graham EA: LATE POISONING WITH CHLOROFORM AND OTHER ALKYL HALIDES IN RELATIONSHIP TO THE HALOGEN ACIDS FORMED BY THEIR CHEMICAL DISSOCIATION. J Exp Med. 1915 Jul 1;22(1):48-75. [19867902 ]
  5. Langfermann C, Klementz D, Sierts-Herrmann A, Poschadel B, Sagunski H, Hosch C, Horn K, Reichmuth C, Baur X: [Study on the potential impact of bromomethane on medicinal products following simulated container fumigation]. Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz. 2007 Apr;50(4):492-9. [17387439 ]
  6. FREW WD: Rectal tribrom-ethanol (avertin, bromethol) in eclamptic toxaemia. Can Med Assoc J. 1953 Sep;69(3):254-7. [13082465 ]
  7. Catto C, Charest-Tardif G, Rodriguez M, Tardif R: Accounting for the impact of short-term variations in the levels of trihalomethane in drinking water on exposure assessment for epidemiological purposes. Part II: biological aspects. J Expo Sci Environ Epidemiol. 2013 Jan-Feb;23(1):60-6. doi: 10.1038/jes.2012.88. Epub 2012 Sep 12. [22968351 ]
  8. Wang GS, Deng YC, Lin TF: Cancer risk assessment from trihalomethanes in drinking water. Sci Total Environ. 2007 Nov 15;387(1-3):86-95. Epub 2007 Aug 28. [17727920 ]
  9. Narotsky MG, Best DS, McDonald A, Godin EA, Hunter ES 3rd, Simmons JE: Pregnancy loss and eye malformations in offspring of F344 rats following gestational exposure to mixtures of regulated trihalomethanes and haloacetic acids. Reprod Toxicol. 2011 Jan;31(1):59-65. doi: 10.1016/j.reprotox.2010.08.002. Epub 2010 Sep 17. [20850520 ]
  10. Rodrigues PM, Esteves da Silva JC, Antunes MC: Factorial analysis of the trihalomethanes formation in water disinfection using chlorine. Anal Chim Acta. 2007 Jul 9;595(1-2):266-74. Epub 2006 Dec 23. [17606009 ]
  11. Zsolnai T: [Tribrom-nitromethan--a new disinfectant of high efficiency (author's transl)]. Zentralbl Bakteriol Orig A. 1973 Oct;224(4):496-502. [4150117 ]
  12. Saghir SA, Ghanayem BI, Schultz IR: Kinetics of trihalogenated acetic acid metabolism and isoform specificity in liver microsomes. Int J Toxicol. 2011 Oct;30(5):551-61. doi: 10.1177/1091581811414213. Epub 2011 Sep 20. [21933969 ]
  13. Weaver WA, Li J, Wen Y, Johnston J, Blatchley MR, Blatchley ER 3rd: Volatile disinfection by-product analysis from chlorinated indoor swimming pools. Water Res. 2009 Jul;43(13):3308-18. doi: 10.1016/j.watres.2009.04.035. Epub 2009 May 3. [19501873 ]
  14. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  15. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  16. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  17. Wikipedia. Bromomethane. Last Updated 27 May 2009. [Link]
  18. Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Bromomethane. U.S. Public Health Service, U.S. Department of Health and Human Services, Atlanta, GA. 1992. [Link]
  19. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  20. Wikipedia. Potassium bromide. Last Updated 9 June 2009. [Link]
  21. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
  2. Wikipedia. Bromomethane. Last Updated 27 May 2009. [Link]
  3. Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Bromomethane. U.S. Public Health Service, U.S. Department of Health and Human Services, Atlanta, GA. 1992. [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
  2. Wikipedia. Bromomethane. Last Updated 27 May 2009. [Link]
  3. Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Bromomethane. U.S. Public Health Service, U.S. Department of Health and Human Services, Atlanta, GA. 1992. [Link]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
  2. Wikipedia. Bromomethane. Last Updated 27 May 2009. [Link]
  3. Agency for Toxic Substances and Disease Registry (ATSDR). Toxicological Profile for Bromomethane. U.S. Public Health Service, U.S. Department of Health and Human Services, Atlanta, GA. 1992. [Link]